Document Type : Research Article

Authors

1 Young Researchers and Elites Club, North Tehran Branch, Islamic Azad University, Tehran, Tehran, Iran.

2 Department of Biosystems Engineering, School of Agriculture, University of Tarbiat Modares, P. O. Box: 14115-111, Tehran, Tehran, Iran.

3 School of Environment, College of Engineering, University of Tehran, P. O. Box: 1417853111, Tehran, Tehran, Iran.

4 Faculty of Chemistry, Shahroud University of Technology, P. O. Box: 3619995161, Shahroud, Semnan, Iran.

5 C1 Water Industries LLC, Dubai Industrial City, Dubai, United Arab Emirates.

Abstract

The presence of increasing concerns and enforcement of growing regulations over environmental pollution are nowadays at play. The pollution arising from mineral oils is among the major concerns. With the gradual reducation of the world oil reserves, an increasing pressure comes into play for finding sustainable alternatives. Being appealing alternatives, vegetable oils consist of different fatty acids; however, they cannot be applied directly to internal combustion engines owing to their poor oxidation stability and high pour point value. Biolubricants are considered to be a new generation of lubricants, which are renewable and biodegradable and are produced from the chemical modification of vegetable oils. There are few studies investigating the feasibility of using the mixture of fatty acids as biolubricant feedstock. In this study, epoxidation, oxirane ring opening with palmitic acid and p-Toluenesulfonic acid, esterification reaction with octanol, and reaction of the remaining hydroxyl group with stearic acid were applied to modify the mixture of oleic and linoleic fatty acids and produce biolubricant. For this purpose, the IR spectrums of each epoxide, monoester, diester, and triester products were obtained and analyzed. At the end of the experiments, monoester, diester, and triester were obtained with 94 % yield, with 96 % yield, and with 98 % yield, respectively. Eventually, the final product was found with physicochemical properties comparable with the physicochemical properties of the lubricant standard ISO VG10.

Keywords

Main Subjects

  1. Zulkifli, N.W.M., Kalam, M.A., Masjuki, H.H., Shahabuddin, M. and Yunus, R., "Wear prevention characteristics of a palm oil-based TMP (trimethylolpropane) ester as an engine lubricant", Energy, Vol. 54, (2013), 167-173. (https://doi.org/10.1016/j.energy.2013.01.038).
  2. Salimon, J., Salih, N. and Yousif, E., "Biolubricants: Raw materials, chemical modifications and environmental benefits", European Journal of Lipid Science and Technology, Vol. 112, No. 5, (2010), 519-530. (https://doi.org/10.1002/ejlt.200900205).
  3. Almasi, S., Ghobadian, B., Najafi, G. and Dehghani-Soufi, M., "A review on bio-lubricant production from non-edible oil-bearing biomass resources in Iran: Recent progress and perspectives", Journal of Cleaner Production, (2021), 125830. (https://doi.org/10.1016/j.jclepro.2021.125830).
  4. Dehghani-Soufi, M., Ghobadian, B., Atashgaran, M., Mousavi, S.M. and Najafi, G., "Biolubricant production from edible and novel indigenous vegetable oils: Mainstream methodology, and prospects and challenges in Iran", Biofuels, Bioproducts and Biorefining, Vol. 13, No. 3, (2019), 838-849. (https://doi.org/10.1002/bbb.1953).
  5. Mobarak, H.M., Mohamad, E.N., Masjuki, H.H., Kalam, M.A., Al Mahmud, K.A.H., Habibullah, Md. and Ashraful, A.M., "The prospects of biolubricants as alternatives in automotive applications", Renewable and Sustainable Energy Reviews, Vol. 33, (2014), 34-43. (https://doi.org/10.1016/j.rser.2014.01.062).
  6. Bashiri, S., Ghobadian, B., Dehghani-Soufi, M. and Gorjian, S., "Chemical modification of sunflower waste cooking oil for biolubricant production through epoxidation reaction", Materials Science for Energy Technologies, Vol. 4, (2021), 119-127. (https://doi.org/10.1016/j.mset.2021.03.001).
  7. Gunstone, F., Rapeseed and canola oil production, processing, properties and uses, CRC Press, (2004). (https://www.wiley.com/en-us/exportProduct/pdf/9781405147927).
  8. Fox, N.J. and Stachowiak, G.W., "Vegetable oil-based lubricants-a review of oxidation", Tribology International, Vol. 40, No. 7, (2007), 1035-1046. (https://doi.org/10.1016/j.triboint.2006.10.001).
  9. 9. Mehdi, S., Asghari, A., Ghobadian, B. and Dehghani-Soufi, M., "Conversion of Pistacia atlantica mutica oil to trimethylolpropane fatty acid triester as a sustainable lubricant", Biomass Conversion and Biorefinery, Vol. 10, No. 1, (2020), 139-148. (https://doi.org/10.1007/s13399-019-00452-y).
  10. Rudnick, L.R., Synthetics, mineral oils, and bio-based lubricants: chemistry and technology, CRC Press, (2020). (https://doi.org/10.1201/9781315158150).
  11. Honary, L. and Richter, E., Biobased lubricants and greases: Technology and products, Vol. 17., John Wiley & Sons, (2011). (https://media.wiley.com/product_data/excerpt/89/04707415/0470741589-42.pdf).
  12. Almasi, S., Ghobadian, B., Najafi, G. and Dehghani-Soufi, M., "A novel approach for bio-lubricant production from rapeseed oil-based biodiesel using ultrasound irradiation: Multi-objective optimization", Sustainable Energy Technologies and Assessments, Vol. 43, (2021), 100960. (https://doi.org/10.1016/j.seta.2020.100960).
  13. Dehghani-Soufi, M., Ghobadian, B., Mousavi, S.M., Najafi, N. and Aubin, J., "Valorization of waste cooking oil based biodiesel for biolubricant production in a vertical pulsed column: Energy efficient process approach", Energy, Vol. 189, (2019), 116266. (https://doi.org/10.1016/j.energy.2019.116266).
  14. Sharma, R.V. and Dalai, A.K., "Synthesis of bio-lubricant from epoxy canola oil using sulfated Ti-SBA-15 catalyst", Applied Catalysis B: Environmental, Vol. 142, (2013), 604-614. (https://doi.org/10.1016/j.apcatb.2013.06.001).
  15. Chowdhury, A., Debarati M. and Biswas, D., "Biolubricant synthesis from waste cooking oil via enzymatic hydrolysis followed by chemical esterification", Journal of Chemical Technology & Biotechnology, Vol. 88, No. 1, (2013), 139-144. (https://doi.org/10.1002/jctb.3874).
  16. Salimon, J., Salih, N. and Yousif, E., "Biolubricant basestocks from chemically modified ricinoleic acid", Journal of King Saud University-Science, Vol. 24, No. 1, (2012), 11-17. (https://doi.org/10.1016/j.jksus.2010.08.008).
  17. Sabzimaleki, M., Ghobadian, B., Farsibaf, M.M., Najafi, G., Dehghani-Soufi, M. and Ardebili, S.M.S., "Optimization of biodiesel ultrasound-assisted synthesis from castor oil using response surface methodology (RSM)", Chemical Product and Process Modeling, Vol. 10, No. 2, (2015), 123-133. (https://doi.org/10.1515/cppm-2014-0013).
  18. Biermann, U. and Metzger, J.O., "Synthesis of alkyl‐branched fatty acids", European Journal of Lipid Science and Technology, Vol. 110, No. 9, (2008), 805-811. (https://doi.org/10.1002/ejlt.200800033).
  19. Salimon, J., Salih, N. and Yousif, E., "Synthetic biolubricant basestocks from epoxidized ricinoleic acid: Improved low temperature properties", Kemija u Industriji: Journal of Chemists and Chemical Engineers, Vol. 60, No. 3 (2011), 127-134. (https://www.researchgate.net/publication/50247430_Synthetic_Biolubricant_Basestocks_from_Epoxidized_Ricinoleic_Acid_Improved_Low_Temperature_Properties).